Since neither the OP, nor the comments give them, I'd like to have a few examples of high quality expensive shoes ... If anyone has suggestions, please enlighten us.
Originally for hiking, but they have also seen daily service as winter boots. Been very pleased with them for both purposes, and they're still as good as new. (As a student, this was a pretty big investment for me, but I'd definitely do it again!)
I have some Y-3 fashion sneakers that I've been wearing pretty often for 5+ years and they are still in good condition (when I bother to clean them, anyway). Maurizi or Rossetti shoes seem to be holding up pretty well, too.
On the other hand, originally expensive and equally Italian Malo shoes (granted, I got them at Filene's Basement for pennies on the dollar) seem to be designed purely to look at, but not to actually wear outside.